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3β,5α,9α,14α-TETRAHYDROXYERGOSTA-7,22(E)-DIEN-6-ONE

Year of first isolation: 1998
Formula:C28H44O5
Molecular weight:460
Occurence in plants:
Pleurotus ostreatus [Fungi] » Images of Pleurotus ostreatus Wikipedia: Pleurotus ostreatus [Fungi]
Pholiota nameko [Fungi] » Images of Pholiota nameko Wikipedia: Pholiota nameko [Fungi]
Occurence in animals:
 
3β,5α,9α,14α-TETRAHYDROXYERGOSTA-7,22(E)-DIEN-6-ONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(C)C=CC(C)C1CCC2(C1(CCC3(C2=CC(=O)C4(C3(CCC(C4)O)C)O)O)C)O
Isomeric SMILES
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C1[C@]2([C@](C[C@H](C1)O)(C(=O)C=C1[C@@]2(CC[C@]2([C@]1(CC[C@@H]2[C@H](C)/C=C/[C@@H](C(C)C)C)O)C)O)O)C » JSMol: View in 3D
IUPAC Name(3S,5R,9S,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5,9,14-tetrahydroxy-10,13-dimethyl-2,3,4,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID10575956
InChiKey
[ ChemIDPlus: search ]
RLODFSODJNFIMP-STGSRIEASA-N
InChIInChI=1S/C28H44O5/c1-17(2)18(3)7-8-19(4)21-10-12-26(31)22-15-23(30)28(33)16-20(29)9-11-25(28,6)27(22,32)14-13-24(21,26)5/h7-8,15,17-21,29,31-33H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,21+,24+,25+,26+,27+,28-/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z338 [M - 4H2O], 263 [M - 4H2O - side-chain]
HR-MS442.3095 [M - H2O]+, C28H42O4 requires 442.3083

CARBON NMR

PROTON NMR

C5D5N
0125.7
0231.3
0366.6
0437.8
0579.6
06199.3
07122.1
08158.9
0977.2
1042.8
1131.0
1228.5
1347.3
1486.2
1527.4
1628.0
1750.5
1816.6
1920.2
2040.4
2121.5
22135.2
23132.4
2443.1
2533.3
2619.9
2720.2
2817.8
C5D5N
01-Ha2.70 (ddd, 14.0, 14.0, 3.8)
01-He 
02-Ha 
03-He4.61 (m)
03-OH6.36 (d, 4.8)
04-Ha2.82 (dd, 12.0, 5.3)
04-He 
05-OH8.45 (s)
07-H6.25 (s)
09-OH6.81 (s)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.73 (s)
19-Me1.13 (s)
20-H2.13 (m)
21-Me1.09 (d, 6.6)
22-H5.26 (dd, 15.4, 8.1)
23-H5.31 (dd, 15.4, 7.3)
24-H 
25-H 
26-Me0.85 (d, 7.0)
27-Me0.86 (d, 6.6)
28-Me0.94 (d, 7.0)

PHYSICAL PROPERTIES

M.P. 
[α]D19- 22.7 ° (c 0.04; CHCl3)
IR (CHCl3) ν max (cm-1)3354, 1687
UV (MeOH) λ max (log ε)225 (3.9) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationYAOITA, Y. et al. (1998) Chem. Pharm. Bull. 46, 944-950 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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